3-(2-吲哚基)-2-丁烯酸甲酯 | 143618-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-(2-吲哚基)-2-丁烯酸甲酯
• 英文名称: methyl indolyl-2-butenoate
• 英文别名: methyl 3-(2-indolyl)-2-butenoate；methyl (E)-3-(1H-indol-2-yl)but-2-enoate
• CAS: 143618-89-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: YVAJDFCUDOPNCC-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-吲哚基)-2-丁烯酸甲酯 在 sodium hydroxide 、 PPA 、 二苯基膦叠氮化物 、 盐酸羟胺 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 乙腈 、 xylene 为溶剂， 反应 38.5h， 生成 t-Boc-Trp-P-1
  参考文献：
  名称：

  Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2

  摘要：

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.

  DOI：

  10.1021/jo00048a026
• 作为产物：
  描述：

  phenyl 3-[1-(benzenesulfonyl)indol-2-yl]but-2-enoate 在 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 12.17h， 生成 3-(2-吲哚基)-2-丁烯酸甲酯
  参考文献：
  名称：

  Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2

  摘要：

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.

  DOI：

  10.1021/jo00048a026

文献信息

• The New Appraoch to Antibiotic Carbazomycins. The Formal Total Synthesis of Carbazomycin A and B
  作者：Satoshi Hibino、Akiko Tonari、Tominari Choshi、Eiichi Sugino

  DOI：10.3987/com-92-s54

  日期：——

  Deoxycarbazomycin B has been synthesized in a four step sequence. The key reaction has been the thermal electrocyclic reaction of 1,3,5-hexatriene system involving the indole 2,3-bond.
• HIBINO, SATOSHI;SUGINO, EIICHI;OGURA, NAOKI;SHINTANI, YOHKO;SATO, KOHICHI, HETEROCYCLES, 30,(1990) N, C. 271-273
  作者：HIBINO, SATOSHI、SUGINO, EIICHI、OGURA, NAOKI、SHINTANI, YOHKO、SATO, KOHICHI

  DOI：——

  日期：——
• Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2
  作者：Satoshi Hibino、Eiichi Sugino、Takeshi Kuwada、Naoki Ogura、Kohichi Sato、Tominari Choshi

  DOI：10.1021/jo00048a026

  日期：1992.10

  Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyrido[4,3-b]indole system have been newly synthesized. The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole [b] bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.